Several evolutionarily relevant sources of individual differences in face preference have been documented for women. Here, we examine three such sources of individual variation in men's preference for female facial femininity: term of relationship, partnership status and self‐perceived attractiveness. We show that men prefer more feminine female faces when rating for a short‐term relationship and when they have a partner (Study 1). These variables were found to interact in a follow‐up study (Study 2). Men who thought themselves attractive also preferred more feminized female faces for short‐term relationships than men who thought themselves less attractive (Study 1 and Study 2). In women, similar findings for masculine preferences in male faces have been interpreted as adaptive. In men, such preferences potentially reflect that attractive males are able to compete for high‐quality female partners in short‐term contexts. When a man has secured a mate, the potential cost of being discovered may increase his choosiness regarding short‐term partners relative to unpartnered men, who can better increase their short‐term mating success by relaxing their standards. Such potentially strategic preferences imply that men also face trade‐offs when choosing relatively masculine or feminine faced partners. In line with a trade‐off, women with feminine faces were seen as more likely to be unfaithful and more likely to pursue short‐term relationships (Study 3), suggesting that risk of cuckoldry is one factor that may limit men's preferences for femininity in women and could additionally lead to preferences for femininity in short‐term mates.